


won't you please cry pretty for me?

by siriuslyuptonogood



Series: Good Boys Do Cry [1]
Category: teen wolf - Fandom
Genre: Alternate Universe - BDSM, Dom Stiles Stilinski, Dom/sub, F/M, M/M, Non-Sexual Age Play, Non-Sexual Intimacy, Non-Sexual Submission, Professional Dom Stiles Stilinski, Spanking, Sub Derek Hale, Sub Isaac Lahey
Language: English
Status: Completed
Published: 2020-02-02
Updated: 2020-02-02
Packaged: 2021-02-27 22:47:29
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 8,946
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22533481
Author URL: https://archiveofourown.org/users/siriuslyuptonogood/pseuds/siriuslyuptonogood
Summary: Stiles has loved to make pretty boys cry since he made Jackson Whittemore sob in an empty locker room during his freshman year of high school. There's nothing in the world that gets him going like knowing he caused the tears running down some pretty boy's face. But what about when he meets one pretty boy who, no matter how hard he tries, just won't cry for him?
Relationships: Chris Argent/Derek Hale/Peter Hale, Chris Argent/Peter Hale, Derek Hale/Stiles Stilinski, Isaac Lahey/Stiles Stilinski, Lydia Martin/Jackson Whittemore, Stiles Stilinski/Jackson Whittemore
Series: Good Boys Do Cry [1]
Series URL: https://archiveofourown.org/series/1621288
Comments: 23
Kudos: 382





	won't you please cry pretty for me?

**Author's Note:**

> Hello, hi.  
> A warning: I wrote 5k of this and Derek hadn't even shown up yet. But, it's also a series and I've already written two more installments, both of which feature Derek MUCH more. So, even though this doesn't seem that Stereky, bear with me.

Stiles was fifteen when he realized how much he liked to make pretty boys cry. The first, Jackson Whittemore, was a bully who, Stiles learned, really got off on being humiliated. It had happened by accident first. Jackson had cornered him in the locker room, thinking he could shove around this scrawny freshman and Stiles had just lost it, shoved him first, which only got him slammed back into a locker, but then it'd been words, telling Jackson how useless he was, how he was a brain dead jock who was just a pretty face and would peak in high school. And then he noticed the older boy sporting a bulge and it's just fueled him. Jackson had started to moan and whimper softly when Stiles started to comment on his dick, only getting harder and louder when the smaller boy had started to rub him through his jeans. 

Jackson had come with a sob and Stiles felt something for those tears running down his beautiful face. He took a picture, called himself from Jackson’s phone, and left him still recovering against the lockers. He'd never felt more powerful in his life. Jackson laid off him after that, especially after a repeat performance where Stiles jacked him off while whispering all those things he knew the boy wanted to hear right in his ear. This time, though, they were in Jackson's bedroom in his huge empty house, parents never home, and Stiles had read enough to know that he shouldn't have left right after the first time. So he never did again. Always stayed until Jackson was coherent again. 

They kept it up regularly until Jackson left for college and then still on breaks between. Even after Stiles moved to New York on a partial ride scholarship to study Journalism at NYU and stopped coming home so he could work, Jackson still came to him.

For the first three years, Stiles worked on campus, cleaning after hours. He worked any shift he could at a coffee shop just off-campus. He cleaned houses on the weekends. And he didn't have to take out loans or have to ask his dad for money. That was very important to him. He was going to make his own way in the world without putting the burden on his dad.

New York offered him way more than Beacon Hills ever had. He'd scoped out the clubs as soon as he had gotten there. He went to a few, but the best one, the one everyone talked about, the Violet Martin, was twenty-one and up. He assumed it was about alcohol. He didn't drink. Hadn't ever felt like it after seeing his dad struggle after his mom died. And he definitely didn't like the idea of mixing kink and alcohol. So he waited to go to where he really wanted to go.

He started his 21st birthday at the DMV. Got his brand-new driver's license, then had an early dinner with a couple of his friends where he had his first legal drink (a beer) and then he got ready for the club. 

It was everything Stiles had ever wanted and more. He ordered himself soda water with lime and walked around, just watching. There were active scenes going on all over the club. He watched a few, wandered, then leaned against the bar to text Jackson. 

_ Finally at Violet Martin. Can just imagine tying you up to a cross, naked. Facing out so everyone can see your pathetic little cock and how hard it gets when I smack it with my crop.  _

The message was read immediately, then for a long time only the little dots. They disappeared a few times, but after almost a full minute if typing, Jackson finally replied. _Fuck off, Stilinksi._

It made Stiles snort. If they were together, he'd have beaten more words out of him, but alas. There was a whole country between them. 

_ What a bad little boy. If you weren't such a pathetic thing that got off on it, I'd beat your ass purple.  _

His phone was ringing immediately. 

"Hey, you," Stiles said, smiling. 

"You're the worst. I'm at a fucking dinner." 

"Poor baby." 

"Stiles." Whine. Stiles secretly loved it, but he always punished Jackson for whining. 

"Tragic for you, little boy. Bet you're in the bathroom, locked in a stall, wanting to yank on that pathetic little dick of yours." 

"Please, Stiles. Please." 

"No fucking way. Take some breaths and get back out to your dinner." 

Another whine, this time no words. 

"Better stop that right now. Don't think I won't make you whup yourself right there in the bathroom. You wearing the black or brown belt?"

He heard Jackson take a deep breath and let it out before mumbling his reply. "Brown." 

"My favorite. Almost wanna hear it snap against your backside." 

Jackson groaned. "Please." 

"Alright, alright. Got anything to say to me before I hang up?" 

"Uh... oh. Shit. Happy Birthday, Stiles." 

Stiles smiled. "If you were here, I'd deliver every one of my birthday spanks with your own belt. And then an extra, of course." 

Just another groan and the sound of Jackson's breath. He was really worked up. Good. 

"Be a good boy, Jacks," Stiles said, then hung up. He smiled and tucked his phone in his pocket. 

Jackson wasn't his. Not permanently anyway. They didn't click outside of the kink. And, if he was honest, humiliation just didn't do it for Stiles. He trusted Jackson. Loved him, even, wanted to make him feel good, and it was always worth it to see him cry.

"Hey," a voice said, sitting down on the stool next to Stiles. Stiles looked over to see a woman with long, red hair, green eyes, and a sharp, red lip. She was dressed in a blue floral summer dress with a blue wrap around her shoulders.

"Didn't mean to eavesdrop, but you've sure got an energy I admire. That your sub on the phone?" she said, smiling as she leaned an elbow on the bar. 

"Oh, no, well... kind of. He was my first. Mostly just friends now. But we play when we can get together." 

The woman nodded, then held out her hand. "I'm Lydia," she said. 

He took it and smiled. "Stiles." 

"You looking to play tonight, Stiles? Heard it's your birthday, " 

Stiles' smile faltered. He did. But not with her. Which seemed mean to say and she seemed interesting. He didn't want to offend her. 

She laughed and, as if knowing what he was thinking, leaned forward and touched his arm. "Not with me, handsome. I do not bottom. But know a boy who might be right up your alley." 

Stiles sighed, relieved, then nodded. "Okay,"

Lydia smiled and leaned back, leaning back against the bar. She got the attention of the bartender. 

"Have Isaac come out here," she said when he came over and he nodded. 

Stiles found himself wondering about Isaac as they waited. Lydia spoke to him, but he was preoccupied right up until this most beautiful boy stopped in front of them. He was tall and slender with a head of curls and deep blue eyes. He had an intoxicating smile with dimples that Stiles just wanted to poke his fingers into. See how deep they went. 

"Isaac, honey, this is Stiles. It's his birthday," Lydia said and Isaac turned the smile on Stiles. 

"Happy Birthday," he said and god, Stiles just knew he'd sound so beautiful crying. "I think I've seen you around. Maybe at Buck's? I work the door on Tuesdays and Thursdays."

Stiles smiled. "I'm there a lot. Biding my time until I could come here." 

"You have such confidence for a dom so young," Lydia said, impressed. "I'll let you two get acquainted." She slid off the stool and ruffled Isaac's hair. "Let Boyd know if you want a room, honey. Nice to meet you, Stiles."

Stiles waved, barely able to keep his eyes off Isaac. 

"So, what do you like, Stiles? Isaac asked and Stiles tilted his head to the side, smiling a little. 

"I like to make pretty boys cry," he said. 

Isaac's eyes lit up. "How?"

"Not picky. No blood. No piss. But otherwise, I like to let the boy tell me what he needs, especially when we're getting to know each other." 

Isaac nodded, considering for a few seconds before he said, "this boy needs a spanking." 

Stiles held out his hand, waited until Isaac had taken it before he gently stroked down the inside of Isaac's forearm with the fingers of his other hands. 

"A been bad spanking or a letting go spanking?" Stiles asked, voice very soft. 

Isaac let out a shaky breath, watching Stiles' fingers and then said, "letting go. M'a good boy." 

Stiles smiled. "You look like you're a good boy, Isaac. How about you let me give you the spanking you need?" 

Isaac swallowed and nodded. "Please... uh, sir."

"Just Stiles is fine for now, pal. You want me to snag a station or do you want to ask for a room. I know letting go spankings can be very emotional."

"Room, room. I'll, uh, get it." Isaac turned back to look at the bartender, hadn't even managed to say anything before there was a key card in his hand. 

"Number 5. Be safe," the bartender, a big, hulking man with dark skin and serious eyes who Stiles decided must be the Boyd Lydia mentioned, said, giving Stiles a look. Stiles was pretty sure this man could tear him in half. Would if he did wrong by Isaac who seemed to work there. He wondered if Lydia worked there too, what she did. 

Stiles stood and offered Isaac his hand. "You'll have to show me where to go." Isaac nodded and led him back through the crowd to a door marked private rooms. It let out into a dim, but warmly lit hall. Isaac headed to room five but was shaking too much to unlock the door. 

"Hey, it's alright, I got it," Stiles said gently, wrapping his arm around Isaac's waist. He took the card and slid it through the slot. The lights came on when the door opened. There was a bed, neatly made, a couple of chairs, a bench, a table tucked in the corner with a mini-fridge, and an ensuite. It was nice, cozy. Stiles let go of Isaac and shut the door behind him. 

"Hey, hey, hold on there pal," he said when Isaac started to fumble with his clothes. "Let's talk a minute first, okay?" 

Isaac paused, but nodded, letting himself be led to sit on the bed. Stiles sat next to him. 

"Can you tell me your limits?" 

"Uh, electricity. Belts. Blood. Penetration. I don't like to be... uh touched on my..." 

"Cock? Balls either?" 

Isaac nodded. 

Stiles gently rubbed his shoulder. "So, just a spanking. That's fine. I didn't expect to play tonight, so I didn't bring anything with me. I'm fine with that. I like using just my hand to start out, but if you think you'll need more and can get something else to use, that's fine too." 

"Hand is good." 

Stiles smiled. "Stoplight safe words?" 

A nod. 

"Can I give you a hug?" 

Isaac hesitated, but then nodded. He was still at first, then melted as Stiles gently rubbed his back. 

"The first time with anybody can be scary, but I'm going to take good care of you. I promise. And not just because I'm pretty sure Boyd would rip me into unidentifiable pieces." 

"I like... to uh snuggle after," Isaac said. 

"Oh good. Me too. Nothing better than snuggling with a freshly spanked boy, in my opinion. I'll take care of you. Ready?" 

Isaac nodded and stood. He gripped the hem of his shirt. "Clothes?" 

"Keep them on for today," Stiles replied, "I'm going to take your pants and underwear down, but I don't think you need to be naked to have a proper letting go spanking. That okay?" 

Isaac nodded. He let Stiles grab his hips and position him. 

"Can you put your hands on your head for me, pal? Let me get these pants down." 

"You're gonna take them down?" Isaac asked, surprised.

"Yep. That alright?" 

Isaac nodded, face turning a little pink, though he did let out a little smile. "Yeah. It's... kinda... Daddy stuff." 

Stiles couldn't help but smile. "Is it? Well, I guess I can see that. You like it?" 

Isaac nodded again, biting his lip. "I usually have to do it myself. But... I like that you're doing everything and I don't have to." 

"You wanted to let go. I think it helps to not have to take down your own pants," Stiles explained, "color?" 

"Green," Isaac said. His arms had come back when they'd been talking, but he put them back up and watched as Stiles unbuttoned and unzipped his jeans, tugging them down to his knees. Stiles slipped his fingers into the waistband of Isaac's briefs and tugged them down too. Immediately, Isaac was over Stiles' lap, Stiles' hand resting on his bare ass. 

"Color?"

"Green." 

"Good boy. Tell me if that changes, alright?" 

Isaac nodded, curling his fingers into the bedspread. 

Stiles started out slow, just warming up Isaac's pale skin, turning it pink before he started to spank a little harder. 

Isaac squirmed as the spanks got harder, starting to whine softly and God Stiles loved that sound... swats to the top of the thighs got Isaac's legs kicking and whining louder. 

"I'm going to help you stay still," Stiles said, shifting so he could pin Isaac's legs with one of his own. He delivered a series of hard swats to the underside of Isaac's cheeks and the boy cried out for the first time and then he was loud, yelping and crying and squirming until his body went limp. 

Stiles couldn't help but feel proud that Isaac trusted him enough to just let go. He delivered just a few more swats to the sobbing boy's backside and then stopped to just rub his back.

"You are a very good boy," Stiles said softly after a few minutes, "took that spanking so well." 

Isaac tried to push himself up, but his legs got caught in his jeans and he almost fell, but Stiles caught him. "Hold on a minute." He carefully pushed the jeans down and slipped Isaac's shoes off so both could be left on the floor. 

"You want your briefs back up before you lie down?" He asked softly and Isaac rubbed at his eyes, still crying a bit, and nodded. 

Stiles got the briefs back in place and then helped Isaac to lie down on the bed. He grabbed a bottle of water from the fridge, slipped out of his shoes, and cuddled up with the boy. He smiled when Isaac clung to him and just held him. 

It took a while for Isaac to really come out of it, but eventually, he pulled back a little. 

"How do you feel?" Stiles asked. 

"Sore. But good," Isaac replied, "I'll be ready to get up in just a minute or two. 

"Don't rush," Stiles said, reaching out to brush a hand over Isaac's curls. "Take all the time you need." 

Isaac studied his face for a few seconds. "Don't you want to go back out to the club?" 

Stiles shrugged. "I just got to spank a pretty boy on my birthday. A very good boy. I don't want for much. Maybe more cuddles. But that's up to you. I could also rub some cream into your poor spanked bottom." 

Isaac looked like he wasn't sure what to do for a second, but then he smiled and curled back up against Stiles, resting his head on his chest and letting out a soft sigh at the feeling of fingers massaging his scalp.

And they talked. Just quietly, curled up like that. Stiles felt good, really good. Jackson didn't like this. He needed the aftercare, but only until he'd resurfaced, and then it was over. But Isaac seemed content to just stay there. And then, to Stiles' surprise, the boy fell asleep. So did his arm. But he wasn't willing to disturb Isaac, so he just laid there.

He wasn't sure how long he'd been there, and he'd started to doze off himself when he heard the door open. He started, still a little drowsy, and looked up to see Lydia with Boyd right behind her. 

Lydia looked amused as Stiles tried to sit up only making Isaac cling more. 

"We don't usually enter private rooms, but Boyd was worried about Isaac." 

"And we closed half an hour ago," Boyd added. 

"Shit," Stiles murmured. He reached over to stroke Isaac's cheek. "Hey, pal. Time to wake up." 

Isaac stirred, making soft, grumbling noises as he pressed his face to Stiles' front. 

"Jesus, if you're not the sweetest thing I've ever seen, I don't know what is," he laughed, rubbing the back of Isaac's neck. 

He glanced at Lydia and Boyd. "Help?" 

Lydia laughed and walked over. She sat on the edge of the bed and rubbed Isaac's back. 

"Honey, you gotta wake up. Let Stiles go home. And Boyd wants to go home too. Won't leave without you." 

"Like Stiles," Isaac mumbled, "he does Daddy stuff. N'cuddles real nice." 

Stiles' cheeks got hot at that, but he felt warm and good. 

Boyd laughed, which surprised Stiles, but when he looked up, he decided the smile on his face fit well. Better than the frown. 

"Go get him a pair of sweats, please," Lydia said to Boyd who left. She gathered Isaac's jeans and shoes, carefully folding them. 

Stiles watched her. They seemed like a family, the three of them. He didn't have much of a family, just his dad. He felt a pang of jealousy and carefully sat up, finally causing Isaac to fully stir.

Isaac sat up, rubbing at his eyes and stretching. He fell back on his ass and whined. 

The jealousy vanished immediately, replaced by fondness. He reached out to gently squeeze Isaac's arm. 

"You good, pal?" 

Isaac nodded and smiled. "Better. Thanks.” 

Stiles held his arms out for a hug just as the door opened again and Boyd returned. Isaac wrapped himself around Stiles' middle, hugging him tightly. 

Stiles smiled, feeling warm, good, but eventually, reluctantly, he had to pull back. Isaac stood and took the sweats from Boyd, tugging them on. He had to stifle a yawn, almost falling over, but Boyd wrapped an arm around his waist. 

"Goodnight, Isaac," Stiles said softly. 

"Night Stiles," Isaac replied with a wave before he let Boyd lead him out of the room. 

Stiles moved, putting his feet down on the floor and stretching. 

"You want a job?" Lydia asked. Stiles glanced at her. 

"What?" 

"From the phone call I overheard, and the way Isaac didn't want to let you go, I feel comfortable taking a chance on you. Want a job?" 

"I'm still not sure what kind of job you're offering," Stiles said. 

"You must know we offer the services of professional players by the hour." 

"Well, yeah, but what--oh. Shit. Me?" 

Lydia glanced at him and then laughed. "Probationary basis, of course. We are a classy place. You'd make enough to work the hours you want and live comfortably." 

Stiles wasn't sure. He was so almost done with his junior year, then he'd only have one year left until he had his degree. But being a professional dom? Not something he'd ever thought of, but he liked the idea of it. 

"Can I think about it?" He asked. 

Lydia nodded. She handed him a business card. 

It was a deep purple with gold lettering. Lydia Martin, owner/operator of the Violet Martin, professional dominatrix. Underneath, a phone number and an email. Shit. He'd managed to impress the owner. He almost felt sick. 

He pulled out his wallet to stick the card in and paused when he saw his own card. He made it in a design class and had liked it a lot. It was silly. Handwriting like text on what looked like lined paper. But it worked and it's what he had. 

"For Isaac," he said, "i... don't expect anything from him. I just would like to hear from him tomorrow. Know he's alright." 

Lydia smiled and nodded, taking it and flipping it over in her hand. "Go home. Get some sleep. Let me know in the next couple of days, okay?" 

Stiles nodded. "Thanks," he said. And slid his shoes on before heading out. 

The thing is, Stiles knew before he even got home that he was gonna do it. No question. He got in quietly, went to his tiny closet of a room in the apartment he shared with four other people and stripped down to his boxers. He felt so damn good and he wanted to continue to feel good. So, of course, he was going to say yes. 

Still, he talked about it with Jackson the next day. Who, despite being a complete asshole the whole time, said he should absolutely take the job. Then, Stiles, determining that Jackson was put out from the night before, made him take a wooden spoon to his balls, inner thighs, and asshole until he was sobbing and very, very apologetic. When he finally got off the phone with Jackson, he saw a message from a number he didn't know. Isaac. Telling him he was sore but good. And thanks for a wonderful night. That was when he texted Lydia. 

\---

On the eve of his thirtieth birthday, Stiles was ecstatic. Lydia has been planning a huge party for months Almost all of Stiles' favorite people would be there. He was going to enter his thirties with a big bang. His birthday present from Lydia arrived that morning. For him to get used to it, the card had said, and Stiles hadn't put it down for two hours after opening it. The crop was honestly the most beautiful thing he'd ever seen. Beautiful silver dyed leather braided with black. It flexed nicely. Smelled heavenly, and he knew from the one smack he'd landed on his own thigh, that the tip stung like a son of a bitch. He didn't yet know who had volunteered to take his birthday spanking, but they were going to be so beautiful marked and terribly sore. Just not Isaac. Who did not do leather. 

When Stiles heard the door to the brownstone he shared with Isaac open and close, he put the crop away and headed down to greet him.

Nine years had gone by since he'd taken the job at the Violet Martin. He hadn't regretted a single second of it. He pushed off the guilt of getting a journalism degree only to never use it by starting to run social media for the club, which he got paid for. So he was technically using his degree. And then a few years later, he'd been approached about a weekly column for a massive online BDSM magazine. Which, of course, he said yes to and had been writing _Silver Says_ ever since. Five years into being a regular professional dom at the Violet Martin, he was making enough to buy the brownstone with a five-year mortgage. He convinced Isaac to move in with him so Boyd could ask Erica, a fiery blonde who worked payroll, to move in after three years of dating. Now, at basically thirty, Stiles had a home. He had a family, a great job. Everything he could need. Well, almost. He'd dated some, but no one stuck. Which was alright. He had Isaac, who'd transitioned into being his little somewhere along the way, and he had Lydia, Boyd, and Erica. He had Scott, his best friend from college, and his wife Kira, who was so miserably pregnant with his niece or nephew that everyone was praying for the delivery in the next few days. Stiles had it good. He really did. 

And he remembered that when he stepped down the stairs and Isaac was half out of his work clothes in the middle of the living room, revealing that he had a pair of Spiderman briefs on underneath and that he'd woken up feeling a little bit small. 

Stiles made a mental note to remind big Isaac that he should tell Stiles when he woke up feeling small, and then caught the boy around the waist before he could trip in his mad dash to rid himself of jean and sweater. 

"Hold on there, pal," Stiles said, fond. He helped Isaac with the jeans and then the sweater, leaving the little in just a t-shirt and his little boy briefs. Once that was done, Isaac wrapped himself around Stiles who hugged him back tightly. 

"Take your clothes to the laundry hamper while I make a snack and you can tell me about your day." 

"Snack with you first, Daddy," Isaac said, clinging.

"Clothes first," Stiles said, voice firm. He gave a warning squeeze to Isaac's backside. 

Isaac pouted, like it was the worst thing in the whole world but pulled back and crouched to gather his clothes. Stiles headed to the kitchen.

He knew Isaac would want sweets but seeing as Stiles was planning their own private birthday celebration, he instead cut up two apples and served them with peanut butter. He poured half apple juice and half water into a Captain America sippy cup and set both that and the snack plate at the bar. Isaac liked to sit in the tall chairs when he was little because it made him feel smaller. Stiles stayed standing. 

Isaac hurried in, climbing up into his chair and immediately going for his cup. He drank probably half of it straight away, which made Stiles frown. But he wasn't about to ask little Isaac if big Isaac had had enough water that day. That was a big Isaac conversation. And, depending on the answers to Stiles’ questions, the conversation might also include a hairbrush. 

"How was your day, pal?" Stiles asked when Isaac had eaten a few apple slices. 

"Inventory," Isaac said, "super-duper boring." 

Stiles nodded. He was glad that wasn't one of his duties. "Well, you're home now. With me. And I haven't got anything super-duper boring planned. You know what tomorrow is, right?" 

"Daddy's Birthday!" Isaac said with a mouthful of apple. It was just too cute for Stiles to scold him for talking with his mouth open. 

"Yep, and I thought I could celebrate tonight with just my best buddy in the whole world," Stiles said. 

Isaac's eyes went wide. "Is that me, Daddy?" 

"You, kiddo," Stiles confirmed and Isaac squealed hopping down to hug him tight. 

"What are we gonna do?" Isaac asked when he'd sat back with his snack. 

"Well," Stiles said, leaning on the counter with his elbows, "first Daddy needs a nap. I'm hoping you'll snuggle with me, even if you don't feel tired. I just feel so much better when I'm snuggling my best buddy." 

Isaac nodded, a serious look on his face. "If Daddy needs snuggles, I'll be there." 

"Then we could watch Captain America." 

"Winter Soldier?" 

"That's the one," Stiles said, "then dinner ordered in from our favorite place. We'll sit in the living room and eat it in our pajamas and watch _How to Train Your Dragon_." 

"Noodles with chicken AND Toothless, Daddy?" 

"Absolutely. Then maybe we can read more of our book. I'm very curious about what's going to happen to the hobbits next." 

"That sounds like the best night." Isaac decided. 

Stiles smiled. "Even better than best because I get to spend it with you." 

When they finished the snack, Stiles refilled Isaac's cup, just water this time, making sure the front door was locked and led Isaac upstairs. The boy was asleep minutes after getting all snuggled up. Stiles knew if he'd even suggested that Isaac needed a nap, there would have been a meltdown. But Isaac loved helping out his Daddy, especially with snuggling. 

The rest of the evening went just as planned. Movies, pad thai, and there was even a special surprise, two cupcakes from their favorite bakery, each with a candle (so Isaac could have a wish too). They got through two chapters of The Fellowship of the Ring before Isaac fell asleep. Stiles turned off the light and drifted off, happy in the knowledge that he was going to wake up cuddled with Isaac. 

Except for Isaac, the brat, wasn't there when Stiles woke up. Stiles was alone, stretched out on one side of his California king bed. He sort of hated the thing. Had bought it in the hopes of sharing it with a partner. But so far, he just shared it once or twice a week with Isaac. Most nights, it was just him.

Stiles stared at the ceiling. He knew Isaac was one of the reasons no one had stuck around for too long. He got it. Didn’t blame them. But Isaac was non-negotiable. He loved Isaac fiercely. Isaac was one of his closest friends, his little boy, his sub. He was family. Always would be. Not long after he and Isaac moved in together and decorated the house, Stiles had realized that he wanted to spend his life with Isaac. Isaac had looked at him, tired, covered in paint, but happy, excited. And Stiles just knew. He had so very gently cupped Isaac's face and murmured. "Want you to be mine forever, pal." Isaac had just smiled even brighter and kissed him. 

He was the reason Stiles realized he was poly. That he could love and adore Isaac while still wanting another partner. Isaac was asexual. He wasn't into the hard play that Stiles was, but Stiles could happily give Isaac everything he needed as his dominant. Isaac gave him a lot of what he needed too. He was happy to let Stiles hold him and spoil him, take care of him in any way he could. And when they weren't Daddy and boy or dominant and submissive, they loved the same movies, had similar tastes in music and food, could spend hours talking about video games or comic books. As far as Stiles was concerned, Isaac was his soulmate. He just also knew there was another one out there somewhere. Stiles knew other poly people existed. Had met a few. He just hadn't found the right person yet.

Stiles heard Isaac thundering up the stairs and settled back, pretending to be asleep. The boy stopped in the doorway and crept into the bedroom. He set something on the bedside table and climbed on the bed over Stiles, but he slipped and nearly jammed his knee right into Stiles' soft bits. 

Stiles yelped and quickly rolled Isaac over onto the bed. "Jesus, pal!" 

Isaac looked up at him sheepishly. "M'sorry." 

Stiles couldn't be mad. He just couldn't so he leaned in. "Forgiven for a kiss." 

Isaac smiled and kissed him quickly on the mouth before sitting up. "I got you special birthday donuts!" He shifted so he was crisscross and pointed but didn't make a move to climb over Stiles again. 

Stiles laughed and pushed himself up. He reached over and picked up the small box of donuts. Inside were all chocolate frosted donuts, his favorite, but they'd been decorated with a bit of colored icing to spell "Happy Birthday" across them all. He smiled and picked up the bar that said "rthday" and took a bite, letting out a soft happy moan. 

"Baby, you went all the way to Minnie's for me?" He asked when he'd swallowed. 

Isaac grinned. "It's your birthday, duh."

"You're gonna help me eat these, right? If I eat them all, I'll be sick, but I can’t stop. They are my favorite.” 

Isaac grinned and grabbed the donut that had just exclamation points on it at the end. He bit into it happily.

Stiles smiled and finished his. He watched the other man for a few seconds, then reached out to gently trace a finger across his knee. "Hey baby, you know who is taking my birthday spanking tonight?" 

Isaac's eyes went wide and he shoved the rest of the donut in his mouth. 

Stiles didn't let go, just waited until he had chewed and swallow to gently tap on his thigh. "I won't tell anyone you told me." 

"It's a surprise!" 

"I can pretend to be surprised." 

"Can't." Isaac crossed his arms. 

"Not even if I tickle you?" Stiles asked, reaching out, but Isaac squealed and clamored off the other side of the bed. He peeked up over the edge. 

"Lydia said little boys who ruin surprises get spankings and corner time," Isaac said, voice very small. 

Stiles sat up properly and held out his hands. "I'm sorry, baby. I won't ask again."

Isaac took his hands, climbing onto the bed, and was immediately pulled into Stiles' lap. He relaxed as Stiles gently rubbed his chin against his neck. 

"Like you fuzzy, Daddy," Isaac murmured, letting himself slip into the headspace, relaxing. 

“Me too, bud,” Stiles said, “I think I’m going to keep it this time.” 

“Good,” Isaac decided.

Stiles gently rubbed his hand down Isaac’s arm. “I am going to go get absolutely spoiled today. Massage. Haircut. Mani-pedi. Some shopping. Do you want to come with me?” he asked softly. 

Isaac sighed heavily. “Have to finish inventory,” he said, shifting so he could look at Stiles. He gave him a big smile then. “But then I get to help set up for your party.”

Stiles didn’t let on that he was disappointed that he’d have to spend his day alone. He smiled. “I’m very excited for my party.” 

Isaac smiled. He kissed Stiles, grabbed another donut, and blew a kiss before heading out. Stiles ate two more donuts, then got up, carrying the box downstairs. He was still just in boxers and a t-shirt when he got down there and not long after, Isaac came down wearing tight jeans and a soft sweater. Stiles wanted so badly to shove him over the counter and spank him over those tight jeans, but he knew it would get him all worked up and Isaac had to go to work. Lydia would literally murder him if he sent Isaac to work in any sort of subspace. Especially during inventory. 

So instead, he just hugged his submissive tight and kissed him before he left. 

Stiles shoved a boiled egg from the fridge into his mouth, protein to cut through the sugar, and headed up to take a bath. And he took his damn time, soaking into the calming lavender-scented water. When the water cooled, he wrapped himself up in a towel and lounged on his bed where he lazily got himself off. His orgasm wasn’t the most mind-blowing he’d had in his life, but it was good enough to make his toes curl. He cleaned himself up with the towel and then got dressed in sweats and a soft sweater to head out to do his errands. 

He had his hair appointment first, then went to the nail salon. He treated himself to a burger from his favorite diner downtown, then went shopping before his massage. He was so utterly relaxed when he got home and took a nap. His alarm went off at six and he got up to get dressed. He had a new tailored suit, red. Bolder than he usually went on clothes, but Lydia had convinced him. It was bright red, complete with waistcoat and he wore a stormy blue shirt with it. No tie. He’d never been huge on ties anyway. 

Lydia texted him at seven and he walked out to the curb, sliding into the back of the sleek, black town car, his play bag tucked under his arm.

“Happy Birthday,” She said when he’d joined her. He leaned in to kiss her cheek. 

“Thank you,” he said, “Have I mentioned how much I fucking love you in indigo?” 

She laughed and sat up a little straighter, showing off the almost iridescent indigo suit she had on herself. “Jackson almost wet himself when I walked into the living room.” 

Stiles laughed. Jackson and Lydia had been a huge surprise, but even Stiles had to admit that they painted a pretty picture when she had him on the ground, her high heeled shoe pressed to his face. And they were good together. Sure, Stiles sometimes missed being the one to make Jackson cry, but he wasn’t going to stand in the way of love. And that’s what they’d had since the very beginning. Four years strong and sometime during their trip to Bora Bora in June, Lydia was going to propose. Stiles was the only one who knew. 

“So,” Stiles said with a smile. 

Lydia laughed. “Not telling you.”

Stiles sighed and sank down in his seat. She swatted his arm. 

“Sit up. You’ll wrinkle.” 

Stiles rolled his eyes, playfully. She took him to a French restaurant. The kind that meant he’d be hitting up a fast-food restaurant on the ride home, but he was grateful all the same. 

The restaurant brought him a chocolate cherry mouse dessert with layers of mousse, sponge, cherry, and cream. God, it was good. He wanted to lick the plate, but he remembered where he was.

After, they went to the club. Lydia’s driver left them off to the side so they could go into the back. Stiles put his bag away and glanced around the employee’s lounge. 

“You make sure my boy was fed?” he asked, glancing at Lydia. 

It was Lydia’s turn to roll her eyes. “You know I’ve been his employer long than you’ve been his dominant, right? I have always taken care of him.” 

Stiles felt his face get a little hot. “Sorry,” he said. “I just am so used to making sure he’s taken care of on club nights.” 

“I know,” Lydia said, tone softer. She kissed Stiles’ cheek. “You’re a good Dom, Stiles. And a good Daddy. Don’t worry about your boy tonight. He’s taken care of. Just enjoy your party.” 

Stiles nodded and brushed his hand over his hair. “Will do. You ever gonna tell me who is taking my birthday spanking?” 

Lydia grinned. “Surprise.” And she left. 

Not three minutes after she’d gone out into the main club, Isaac came barreling back into the employee lounge. He tackled Stiles into a hug, and it was only by the grace of God that the two of them didn’t go down to the floor. But Stiles laughed and held him. 

“Was thinking about you all day,” Isaac murmured, “And spending your birthday by yourself. I should have taken the day off.” 

“Nope,” Stiles said, “Everything is good. Want to take me out to my party?” 

Isaac kissed his cheek and nodded practically dragging him out. And everything was perfect. The whole place was decorated in silver for his birthday. It made him smile. Lydia had coined his scene name early on, when she dragged him to a toy store, and he’d fawned over anything shiny and silver. It’d been teasing at first, but he’d grown to love it. And it made buying toys easy. Everything was black, silver, or both. Or brown leather. He liked leather a lot. 

There was a banner over the bar that said “Happy 30th Birthday, Silver!”

“Oh, this is all so lovely,” Stiles said, pulling Isaac close. He let out a soft, happy sound when Isaac wrapped his arms around him, nuzzling his neck. 

The first hour was exhausting. He had to play host. He wanted to watch, to wander, but people wanted to talk to him. First, so they could say happy birthday, but then to catch up. A few people tried to set up appointments with him, but he reminded them that it was his birthday. No business. They needed to email the appointment service for the club. 

He managed to extract himself and head to the bar. He ordered a soda water with lime for himself and a bottle of flat for Isaac, who he had to locate and while he was waiting, he caught sight of a familiar face. Derek Hale. He was tall, solid, had beautiful, dark hair, eyes like green marbles, and an enticing smile. Stiles just watched him as he slowly moved through the room. Stiles startled when Derek caught his eyes and then fucking smiled at him. Fuck. He grabbed his drink from the counter and sipped it, watching as Derek got closer. When finally, there were no other people between then, Stiles noticed, with no small amount of surprise, Derek’s bare neck.

The first time Stiles had ever laid eyes on Derek was Derek’s twenty-fifth birthday almost three years earlier. Stiles had never been so taken with someone so quickly before and he’d watched, mesmerized, as Derek laughed, fucking laughed through both a hand-spanking and paddling that hadn’t looked gentle from the colors his skin had turned. Derek had whined. He’d begged, he’d whimpered and pleaded, and he had cried out, but not one tear had dripped down that pretty face. Stiles had been amazed and immediately curious as to how to make this pretty boy cry. But he’d never gotten the chance because Derek belonged to Chris and Peter Argent. He was theirs, wore their collar proudly at his throat. Until that night, though, when Stiles watched him walk up, no collar, no Chris, no Peter in sight. 

“Happy Birthday,” Derek said with a smile. 

“Thank you. Glad you could come. Haven’t seen you in…” he trailed off, unsure when the last time he’d seen Derek. 

“Peter, Chris, and I have been in Europe since Fall. I came back a few weeks ago. Luckily in time to RSVP to the invitation that had shown up while we were gone,” Derek replied, leaning back against the bar. 

“Just you?” 

Derek nodded. “They wanted to stay. Chris retired from the company when his genius daughter graduated with her MBA and could take over.” 

“He isn’t old enough to be retired,” Stiles replied 

Derek laughed. “What I said. But he’s fifty this year. He started working for his dad’s company when he was sixteen. Retired with over thirty years.” 

Stiles watched him a second. “You’re not wearing a collar,” he said. 

Derek lifted a hand to touch his throat as if he’d forgotten. “They’re still… mine. I’m still theirs’. Always will be. But Chris wants to travel. Peter can take his job with him, but I miss the city too much. Wanted to come home. I’ve always been able to step outside the three of us. Just haven’t.” 

Stiles nodded. “Seems fair.” 

Derek glanced over at him. “It’s me, you know.” 

Stiles frowned. “What?” 

“Lydia said you don’t know who you’re playing with tonight. It’s me,” Derek said, “Figure I’m allowed to say so.” 

Stiles’ eyes lit up. “Are you going to cry for me? For my birthday?” 

Derek laughed and pushed himself away from the bar. “Probably not,” he said, “But don’t take it personally.” 

Stiles watched his retreating back, didn’t notice that Isaac had come up beside him until he was pressed right against him. And Stiles laughed, kissing him. He handed over the bottle of water. 

Derek didn’t cry. 

Nor did he cry the next time they played, this time heavier, with all of Stiles’ favorite leather. Or when he caned him cold. Damn skin split but not even one fuck tear. 

A week after the caning, Derek invited him over for dinner. Cooked for him. They watched movies until two am. 

In one of the club’s private rooms, Stiles made him count a hundred with the belt. And after Derek was so blissed out and just snuggled for hours. Which Stiles loved, don’t get him wrong. But still no tears. 

Soon, they were texting every day. They met up once a week, at least. At their homes or out, it didn’t matter. They went to movies. Isaac tagged along too, and he got on so well with Derek. He fit. God, he fit so well. Stiles just… wanted him. But it felt like he hadn’t quite gotten in yet. Like there was still a wall between the two of them. 

When he texted Derek to ask if he’d be at the club that night – he only had one appointment scheduled – he got a picture back of him, a goofy grin, Peter and Chris crowded into the frame with him. The collar was back. He felt a sense of dread. They were back. Did that mean he would lose Derek? That made him want to curl up under his bed and never come out. He hadn’t even realized how fucking gone on him he was. 

Stiles’ appointment was early. Then he was free. He could choose to take walk-ins if he wanted, just tell the bartender, but he saw Peter sitting by himself in one of the small seating areas that dotted the club floor and went over. He sat across from him and almost frowned at that smug look on Peter’s face. God. He hated him just for the idea that he could take Derek. But Derek wasn’t an object. He couldn’t be taken, not against his will anyway. 

“Stiles,” Peter said, as greeting, “Derek and Chris are back in a room. No idea when they’ll be out again, but they’ve been gone a while.” 

Stiles wanted to say so much. Part of him wanted to beg, wanted to make sure that Peter wasn’t going to cause him this great sadness, but what came out instead surprised him. “How do I make him cry?” 

Peter looked as if he wasn’t sure how to answer and then he laughed, shaking his head. “That depends on you.” 

Stiles blew out a breath, frustrated. “How do _you_ make him cry?” 

“A look, two words, a snap,” Peter replied, breezily. And it couldn’t just be that damn easy. Stiles wanted to ask a million questions. What words? What look? Why did the snap even matter? How did he do it? Why didn’t Derek cry when his ass had been beaten raw like literally everyone else Stiles had ever met? 

He even opened his mouth up to ask, but then he saw Derek and his heart dropped because his eyes were red and his nose pink and fuck, he’d been crying, but now he was smiling and had his arms wrapped around Chris’ body as they walked. Maybe it was him. He wasn’t enough for Derek. There was something lacking in him specifically, something Chris and Peter had that Derek needed. Derek smiled when he saw him, though. And hugged him. Stiles hugged him back, happy to see him, but then Derek was pulled into Peter’s lap and snuggled, and Stiles said he had to go. 

Later that night, as the three of them were on their way out, Peter paused at the bar where Stiles was people watching, waving the other two on ahead.

“Don’t give up,” Peter said, his tone friendly enough, “He’s our boy. But he could be your man, you know.” 

Stiles looked at him, not understanding at first, “A partner,” he said after a second, “Not just a sub.” 

“We have lines we don’t cross with him. And he has had a string of casual relationships and one-night stands. But… he deserves more.,” Peter said. 

“You don’t…?” Stiles asked, frankly surprised. 

Peter raised an eyebrow. “You know the rumors, I’m sure.” 

Stiles nodded after a second, though he knew it hadn’t been a question that required it. Peter was a Hale before he was an Argent. There had always been rumors there. 

“I was adopted, regardless,” Peter said with a toss of his wrist, “But Chris and I love Derek. Adore him. Tease, push, pinch, poke and spank him. But we don’t fuck him. Never have. Never will.” 

Stiles nodded, processing, but when he looked up again, Peter had left. Stiles sighed and leaned against the bar. The last appointment slot of the night was a walk-in and it helped to not think about Derek for a while, but as soon as he was home again and laying in his big bed all by himself, Derek was all he could think about. 

Stiles didn’t give up. 

He tried all his tricks. 

He tried hard. Like he’d tied him up and teased him, when he’d left marks with the crop and the cane all over his body, smacked his balls, his dick, made him bend over and hold his ass open, hitting him right on the asshole a dozen times. He could make Derek whine and keen. He could make him shout, plead, beg. He even managed to make Derek howl and scream. But he just couldn’t get the one thing he wanted above all. 

And then it happened by accident after more than six months. When Stiles hadn’t even been trying, which he guessed was always the way it went. 

It’d started with a few texts. Derek was having a bad day. He’d been frustrated with a case that wasn’t going well all week. And Stiles felt for him, he really did. Derek had graduated from one of the best law schools in the country and then, to the shock of everybody, decided to work as a child advocate. And sometimes it sucked, and it was disheartening. He didn’t blame Derek for being upset sometimes. But when Stiles had called, hoping to convince him to come over for pizza and movies with Isaac, he’d learned exactly how much it was affecting Derek. 

“I’m just so fucking useless, Stiles,” Derek said, “I fucked everything up. I should have been _better_ because now this kid is just going to have to back to his shitty fucking parents instead of the foster family who adores him. Fuck I’m just so frustrated and I’m just so fucking useless.” 

And Stiles hated that. He hated the words coming out of Derek’s mouth. He hated that he was so down on himself for something that wasn’t even his fault. That he was calling himself useless. 

“Stop,” he said, his voice hard. There was a sharp intake of breath on the other side. “You’re not useless and you don’t get to fucking say that about yourself okay? There is no excuse for it. None. Get your ass over here now.” 

“Yes, sir,” Derek replied almost immediately, a quality to his voice that Stiles has never heard before. When the call ended, he wondered if he’d gone too far. 

But Derek showed up all the same. And he was quiet, and Stiles looked at him for a few seconds before he took him by the wrist and lead him up to the bedroom. He sat down on the bed. Derek sat but looked at his hands.

“I apologize if I went too far, but Derek I just care about you so damn much and it makes my blood boil to hear you talk about yourself like that. You are not useless, and it is absolutely unacceptable for you to say that shit about yourself. Got it?” But when Derek only nodded at his lap, Stiles tapped his chin. “Hey, look at me.” 

Very slowly, Derek lifted his head, his eyes wide and full of tears. Stiles swore and cupped his face. “Why the tears, honey?” Because yeah, he wanted the tears, but he needed to know why they were finally happening. Had Stiles fucked up? Had he really gone too far?

Derek bit his lip. “You care about me and I let you down,” he said very quietly after a few quiet seconds. 

And suddenly Stiles understood what Peter had said, a look, two words, and a snap. That was enough to indicate disappointment or displeasure and that’s what it took to make Derek cry. Okay, he still didn’t understand the fucking snap, but the rest made sense, okay?

“You did,” Stiles said, “and I do. But you’re not gonna talk about yourself that way anymore, right?”

Tears spilled down Derek’s cheeks and he shook his head quickly. 

“Good boy.” Stiles brushed his hair back from his forehead, resisting the urge to wipe away the tears. “Next time, I’ll put you over my knee. But for now, why don’t you just lay with me?” 

Derek kicked off his shoes and waited until Stiles had gotten comfortable to join him. He rested his head on Stiles’ chest. 

“I was right,” Stiles said after they’d just been laying there a while and he’d been combing his fingers through Derek’s hair. 

“Bout what?” 

“I just knew that you’d be the prettiest boy I’d ever see cry. Kinda seals the deal for me, really,” Stiles said. 

Derek tilted his head back, green eyes wide, his face open, vulnerable. “Deal?” 

“Yup,” Stiles said with a grin, “I’m absolutely gone on you, Derek Hale.” 

And then Derek cried. Hard. He curled his fingers in Stiles’ shirt and buried his face in his shirt, letting out a slur of hiccupping words that Stiles didn’t understand. 

“Hey, can’t understand you. Can you take a deep breath and say it again?” 

Derek took a few deep breaths. It wasn’t much better the second time, but Stiles at least understood it. And god it made him almost want to cry.

“I love you too, Derek,” he said. And that brought on a whole new round of tears. But Stiles didn’t mind. Just held him tight and told him how fucking beautiful he was. Would, for as long as Derek needed. 

**Author's Note:**

> Hey! Hit me up at siriuslyuptonogood on Tumblr!


End file.
